Organic mercury compounds as



Patented Dec. 1 5, 1942 S PATENT OFFICE ORGANIC MERCURY COMPOUNDS AS DISINFECTANTS Vartkes Migrdichian, Greenwich, Conn., assign to American Cyanamid Company, New Yo; N. Y., a corporation of Maine N Drawing. Application December 3, 1940,

- Serial No. 368,362

in which Ridenotes an organic group attached.

to oxygen by means of a valence of carbon, said group containing, in addition to hydrogen,,at' least one negative substituent, e. g. cyanogen.

'thiocyanogen, halogen, alkyloxy, carbalkoxyl and the like, R: denotes alkyl, aryl, or aralkyl radicals, and R3, R4, R5 and Rs denote hydrogen, alkyl, aryl or aralkyl radicals.

In producing mercury compounds of this type, the acetate salts of said compounds are first prepared by the interaction of a hydroxy compound containing at least one negative substitutent such, for example, as ethylene chlorhydrin, monomethyl glycol ether, monoethyl glycol ether, glycolic nitrile, acetaldehyde cyanhydrin, ethyl lactate and the like, a compound containing an ethylenic linkage such, for example, as ethylene itself, propylene, isobutylene, styrene, and the like, and mercuric acetate.

The acetates thus formed are converted by dilute hydrochloric acid or a sodium chloride solution to the corresponding chloride compounds, and by simple metathesis from the latter and a sodium alcoholate in alcoholic solution these new products may be readily obtained.

The reactions leading to the formation of pchlorethoxyethyl mercury ethoxide, a typical example of the foregoing compounds, may be illustrated by the following equations:

OlCHaCH,OH+C|Hi+H (OCOCHI):

CICHzCHr-O-CHr-CHr-HE-Cl+CHaCOOH 01cmcm-o-cm-cnr-ng-cwm-o-cim As showing the wide diversity of compounds which may be used for the purposes of this invention, the following may be mentioned: p-methoxy-ethyloxyethyl mercury methoxide, p-methoxyethyloxyethyl mercury benzyloxicle, p-ethoxy- 15 Claims. (Cl. 167 22) The present invention relates to new disinethyloxyethyl mercury ethoxide, p-ethoxyethyloxyethyl mercury phenyloxide, fl-ethoxyethylo'xyethyl mercury benzyloxide, fi-chlorethoxyethyl mercury methoxide, p-chlorethoxy'ethyl mercury ethoxide, fi-chlorethoxyethyl. mercury butoxide, -fi-chlorethoxyethyl mercury benzyloxide, cyanmethoxyethyl mercury ethoxide, cyanmethoxyethyl mercury phenyloxide, a-carbethoxyethyloxyethyl mercury ethoxide, p-chlorethoxypropyl mercury methoxide, p' chlorethoxypropyl mercury benzyloxide, p-chlorethoxybutyl mercury methoxide, e-chlorethoxybutyl mercury ethoxide and ,B-chlorethoxyphenylethyl mercury methoxide.

The above class of mercury compounds possess high fungicidal power and have been found particularly valuable for use as dusting disinfectants in combating seed diseases. Excellent control of the fungus diseases of seed corn may be obtained with dust mixtures containing as low as one per cent of the active compound. Other plants whose seeds may be advantageously disinfected in accordance with this invention include ryl, oats, barley, maize, wheat, peas, beans, potatoes, etc;

These new disinfectants are also highly efficacious against plant pests and microorganisms, such as insects, bacteria, moulds and the like, with the result that they may be employed for all purposes of preserving or'disinfecting, for example, the immunizing of seeds, the preservation of wood, the prevention of mildew formation, in the preservation of glue, in insecticidal compositions and the like.

The invention is further illustrated by the fol- I lowing examples.

Example 1 Seed corn, infected by Fusarium, is dusted in the ratio of 1000 to 16 with a mixture consisting of 99 parts by weight of talc and one part by weight of ,B-methoxyethyloxyethyl mercury methoxide of the formula:

CH3OCH2CHzO-CH2--CH2HgOCHs Germination of the fungi spores is prevented.

Example 2 fi-methoxyethyloxyethyl mercury benzyl oxide of the formula:

is used in a manner similar to the procedure of Example 1.

Example 3 One gram of dust consisting of 97 parts by weight of talc and 3 parts by weight of the mercury compound, p-chlorethoxyethyl mercury ethoxide (C1CHzCH2-0 CHzCHz-Hg-OCaH) is placed in a stoppered four-ounce bottle. Fifty corn seeds, Gibberella infected, held in a saclr suspended in the bottle, are exposed to the vapors of the mercury compound for one week. Upon germination of the exposed seeds it is found that the germination of fungi spores is averted.

Example 4 An immunizing agent consisting of one part by weight of a-carbethoxyethyloxyethyl mercury ethoxide land 99 parts by weight of talc is dusted onto seed corn, Diplodia infected, in the proportion of 1.5.

ounces of dust to one bushel of corn. Germination of the fungi spores is prevented.

Example 5 Cyanmethoxyethyl mercury phenyioxide of the formula:

' CNCHPO-CHPCHk-Hg-O-CGHE is used in a manner similar to the procedure of Example 4. r

It is to be understood that the foregoing examples are merely illustrative and that this invention may be applied to the wide variety of organic compounds represented by the general formula given. Also, it is believed that the mercury compounds herein disclosed and the methods of producing the same are "not formerly known.

Although these mercury compounds may be used alone, it is usually preferable to mix them with inert fillers or spreading materials such as talc, bentonite, kieselguhr, fullers earth, pumice, silica, silicates, chalk, etc. These inert materials are preferably in a finely divided state, as are the mercury compounds, and mixtures of the ingredients are easily prepared in any well-known manner. The proportions of the ingredients in the finished dust may be varied widely in accordance with the particular efiects desired and the conditions under which they are to be used. Un= der some circumstances it may be desirable and feasible to apply the present compounds in the form of solutions or suspensions in water or other liquid, and the present invention does not preclude such use.

While the invention has been described with particular reference to specific embodiments, it is to be understood that it is not to be limited thereto but is to be construed broadly and restricted solely by the scope of the appended claims."

I claim:

1 The method of protecting organic materials general formula:

sisting of hydrogen, alkyl, aryl and aralkyl radicals.

2. The method of protecting organic materials subject to attack-by plant pests and microorganisms which comprises treating the said materials with an organic mercury compound of the in which R1 denotes an organic group containing in addition to hydrogen at least one negative substituent, R2 is selected from the group consisting of alkyl, aryl and aralkyl radicals, and R3 and R4 are selected from the group consisting of hydrogen, alkyl, aryl and aralkyl radicals.

3. The method of protecting organic materials subject to attack by plant pests and microorganisms which comprises treating the said materials with an organic mercury compound of the in which R1 denotes an orgapic group containing in addition to hydrogen at least one negative substituent, and R2 is selected from the group consisting of allsyi, aryl and aralkyl radicals.

a. The method of protecting organic materials subject to attack by plant pests and microorganisms which comprises treating the said materials with an organic mercury compound of the general formula:

in which R1 denotes an organic group containing in addition to hydrogen a negative substituent subject to attack by plant pests and microorselected from the group consisting of cyanogen,

thiocyanogen, halogen, allryloxy and carbalkoxyl radicals, and R2 denotes an alkyl radical.

5. The method of protecting organic materials subject to attack by plant pests and microorganisms which comprises treating the said materials with an organic mercury compound of the eneral formula:

i which R1 denotes an organic group containing in addition to hydrogena negative substituent selected from the group consisting of cyanogen, thiocyanogen, halogen, alkyloxy and carbalkoxyl radicals, and R: denotes an aralkyl radical.

6. The method of protecting organic materials subject to attack by plant pests and microorganisms which comprises treating the said materials with an organic mercury compound of the general formula? in which R1 denotes an organic group containing in addition to hydrogen a negative substituent selected from the group consisting of cyanogen, thiocyanogen, halogen, alkyloxy and carbalkoxyl radicals, and R2 denotes an aryl radical.

7. The method of immunizing seed which comprises treating said seed with an organic mer cury compound'oi the general formula;

Ra Ra Rr-o-o- Hg-Ra 8 l in which R1 denotes an organic group contain- .ing in addition to hydrogen at least one negative substituent, R2 is selected from the group consisting of alkyl, aryl and aralkyl radicals, and Ra, R4, R5 and Rs are selected from the group consisting of hydrogen, alkyl, aryl and aralkyl radicals.

8. The method of immunizing seed which comprises treating said seed with an organic mercury compound of the general formula:

in which R1 denotes an organic group containing in addition to hydrogen at least one negative substituent, R2 is selected from the group consisting of alkyl, aryl and aralkyl radicals, and R1 and R4 are selected from the group consisting of hydrogen, allgvl, aryl and aralkyl radicals.

9. The method of immunizing seed which comprises treating said seed with an organic mercury compound of the general formula:

stituent selected from the group consisting of cyanogen, thiocyanogen, halogen, aikyloxy and carbalkoxyl radicals, and R: denotes an alkyl radical. I

11. The method of immunizing seed which comprises treating said seed with an organic mercury compound of the general formula:

in which R1 denotes an organic group containing in addition to hydrogen a negative substituent selected from the group consisting of cyanogem thiocyanogen, halogen, alkyloxy and carbalkoxyl radicals, and R: denotes an aralkyl radical.

12. The method of -immunizing seed which comprises treating said seed with an organic mercury compound of the general formula:

H H m-o-d -d-m-o-m in which R1 denotes an organic group containing in addition to hydrogen a negative sub stituent selected from the'group consisting of cyanogen, thiocyanogen, halogen, alkyloxy and carbalkoxyl radicals, and R2 denotes an aryl radical.

13. The method of immunizing seed which comprises treating said seed with an organic mercury compound of the formula:

14. The method of immunizing seed which comprises treating said seed with an organic mercury compound of the formula:

15. The method of immunizing seed which comprises treating said seed with an organic mercury compound of the formula:

CNCH2OCH2CH:I-IgO-C&H5

VAR'I'KES MIGRDICHIAN. 

